It Was Supposed to be You
by Moonrays and fridays
Summary: After sleeping with Dean for the first time, Rory runs into Jess. A short and sweet oneshot.


The worst part was that her mother didn't understand. She couldn't believe that she didn't understand. This was _Dean_. Her mom loved Dean, and now she was ruining it for them. This was supposed to be special, and Lorelai had ruined it.

She tried calling him, but _she_ answered, Lindsey. Hang up and try not to cry. She grabbed her jacket and stepped out into the cool night, walking briskly to try to stop herself from falling apart. Why was it all going wrong? She walked until she reached the bridge. Her bridge.

And then she saw him. Same jacket, different hair. And a look of pure shock on his face.

"Rory." He jumped out of his skin with surprise, wanting to rush towards her and knowing he'd just scare her away.

"Jess? No. No no no no no!" She whined with anger, "What are you doing here? I'm leaving."

"No, look, don't leave, you're upset. I'll go if you want." He wanted so much for her to talk to him, to look at him. He had so much to say and he'd been a coward up until now.

She burst into tears and he moved towards her, extending his hand. She backed away furiously, "Don't!"

"Sorry." He put up his hands and backed away slowly.

"Why are you here Jess?" She glared at him.

"I was visiting my mom, I came back for the wedding a few weeks ago." He ran his hands through his hair, "I wanted to see you. I meant to see you then but I bottled it. Sat in my car outside Yale for half an hour. What a loser, right?" He almost laughed, uncomfortable but really needing to show her he could be honest.

"Why didn't you get out of your car?" She sat down on the bridge, her feet over the edge, the way they used to sit together.

"I almost did, and then I saw you." He took a deep breath, "you were with Dean, and I figured it wasn't the right time."

"You've changed." She said gently, looking at him, "The old you would have barged in no matter what."

"I'm trying. Someone once told me I had a lot of potential." He smiled, nudging her as he sat down beside her.

"What were you going to tell me?"

"Last week? I was going to rush in, and tell you I was sorry, and that I'd let you down but you could count on me now. That I'd changed. I was going to ask you to run away with me."

She turned white and stuttered.

"Pretty stupid, I know." He smiled softly, "To think you'd be waiting."

"I was waiting, I waited an entire year and heard nothing! No word. No explanation. And now, tonight, of all nights, you're here." She shook her head.

"What was tonight?" He didn't want to know, he knew it couldn't be good. He didn't want to know.

"I slept with Dean." She didn't have to say it was her first time, he could tell.

"Oh." He tried to ignore the kick to the stomach, tried not to picture it. "Wait, isn't he-"

"Married?" She sighed. "Yes."

"Oh, Rory."

"What?" She turned on him, "You can't judge me! You ran away! He loves me! He's always loved me!"

"Then why did he marry her?" He said softly, reaching for her hand ever so slowly, hoping she wouldn't notice.

"Because…because I was with you. Because I left him and took a chance on you, and he…he had to…she tricked him into it." She settled angrily.

"Have you convinced yourself yet? No guy gets forced into marriage, especially when he's nineteen. He wanted to marry her. And he's made you his mistress."

"He has not! We…he's…" She burst into tears again, "This was not the way this was supposed to go."

"Well you could have picked someone who wasn't married." He agreed.

"It was supposed to be you." She vented, staring him straight in the eye, and he suddenly felt like the bottom fell out of his world. "The week before you left, I'd decided it was going to be you. It had to be. And I was just trying to work out the details in my head, the wheres and whens." She snorted to herself quietly "I didn't even make a pro-con list. I just knew."

"I'm so sorry." He whispered. "I really wanted to make things better. I wanted to be better for you. I didn't want to screw your life up too."

"You weren't going to!"

He ignored this altogether, they both knew it wasn't true.

"I'd thought about it too, you know." He smiled crookedly, "I mean, teenage boy, so I wasn't thinking about much else, but, I really wanted it to be special for you. Mine was kinda rubbish."

"Who was it?"

"Some girl in a dark room. Didn't know her name. She was older, I was drunk. And that was that, ya know?"

"That sounds horrible." She shivered, and moved closer.

"That's why I wanted it to be better for you. I…Oh god, with the honesty tonight…I always thought I could pretend with you, that it was my first time too." He looked away, "And if you laugh at me I will actually have to kill you."

She smiled suddenly, and he was hit by the full force of just how beautiful she was.

"I've missed you." He whispered, and wiped a tear track from her cheek.

"I…I'm still mad at you." She said, not unkindly. "But I've missed you too."

He tried to ignore the way his heart was pounding, or the voice in his head that said 'You should have gone to Yale, you should have told her everything, you should have run away with her.'

"So are you…I'm going to regret asking this…" He started, looking resolutely at the water.

"I'm not in love with him." She said simply, "He loves me. He's unhappy with Lindsey. He said he was leaving her. And it's suddenly occurred to me that that's never going to happen."

"Do you really want it to?" His fingers moved closer to hers, ever so slowly.

"Do I want to break up a marriage? No. Am I lonely? Yes."

"That's my fault." He said concretely.

"Yes, it is."

They sat quietly in the darkness for what felt like an eternity, the only sounds those of the water lapping and their quiet, steady breathing.

"Was it any good?" He asked, trying to be funny, but knowing he really shouldn't be torturing himself like this.

"Well, how would I know, really? Not much to compare it to." She shrugged.

"I guess not."

"What about you? You been with anyone whilst you've been flitting around wherever you've been?" She really didn't want the answer to this question, why were they talking about this? Why couldn't they just pretend-

"No."

"Just, no?" She raised an eyebrow, "That's it?"

"I still love you. You know that." He said simply, avoiding her eyes.

And oh, how it got complicated again. How her palms got sweaty and all that ridiculous stuff people associate with romance. How her heart beat faster, but she couldn't tell if it was because she loved him or hated him. How he made her want to scream with his bad timing, and unreliability. How he made her want to make the irrational decision, to throw away the rule book and the lists and just 'be'.

"Wow. What happened to the old Jess? You know, the one with the monosyllables and the never talking about anything to do with feelings?"

"He realised he kept hurting people and had to get his act together." He replied, simple and succinct.

"Wow."

"You keep saying that."

"Well, you keep suprising me." She relented. "What's this about? Is it an apology, what is it? You're not moving back to Stars Hollow?"

"I could. I will. If that's what you want." He began earnestly. "And if you say 'wow' again…"

"You don't want to live here. You want to live in New York."

"I want you. End of story."

"Wo-wza." She corrected herself as he raised an eyebrow, smirking that smile that she used to love.

Insatiable, dangerous. Bad bad boy. Wrong for her. But who was right? The boy she once loved who cheats on his wife? Or this one? The one who she used to stay up all night talking to, the one who knew her soul, who stole her books, who was asking for another chance?

"Where would we have gone?" she asked suddenly, "When you were at Yale, if you'd asked me to run, where would we have run to?"

"I don't think my brain had got beyond the basics. Rent a little place in New York, wake up together every morning, haunt the book shops, go to gigs, eat take-out, fall asleep. Just for the summer at least." He shook his head, "And then you'd go back to Yale and become that overseas journalist, and I'd carry on living where I wanted and working when I needed the money. I just wanted to show you we could work, away from all of this."

"Away from all what?"

"Your mom, and Luke, and Stars Hollow watching our every move, and Dean towering over me, wanting me to fight. That away from everyone we could just be together. Be happy. Just for a while."

She smiled into the darkness, and gently reached for his hand, so familiar. The hand that had held hers and stroked her face and tucked strands of hair behind her ear. She was still scared. He squeezed her hand, begging her to take another chance on him.

"You know, that sounds really nice." She said, as they stared out across the lake, and waited for the next day to begin.


End file.
